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L(-)-Malic acid(CAS No. 97-67-6)

L(-)-Malic acid C4H6O5 (cas 97-67-6) Molecular Structure

97-67-6 Structure

Identification and Related Records

【Name】
L(-)-Malic acid
【CAS Registry number】
97-67-6
【Synonyms】
(S)-(-)-Hydroxysuccinic acid
L-(-)-Malic acid
L-Hydroxysuccinic acid
L-malic acid
【EINECS(EC#)】
202-601-5
【Molecular Formula】
C4H6O5 (Products with the same molecular formula)
【Molecular Weight】
134.08
【Inchi】
InChI=1/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)
【InChIKey】
BJEPYKJPYRNKOW-UWTATZPHSA-N
【Canonical SMILES】
C(C(C(=O)O)O)C(=O)O
【MOL File】
97-67-6.mol

Chemical and Physical Properties

【Appearance】
clear colourless solution
【Density】
1.641g/cm3
【Melting Point】
101-103℃
【Boiling Point】
140℃
【Refractive Index】
-6.5 ° (C=10, Acetone)
【Flash Point】
220℃
【Alpha】
-2 o (C=8.5, H2O)
【Water】
soluble
【Solubilities】
soluble
【Color/Form】
COLORLESS
WHITE TRICLINIC CRYSTALS
【Stability】
Stable at room temperature in closed containers under normal storage and handling conditions.
【HS Code】
29181980
【Storage temp】
Store at RT.
【Computed Properties】
Molecular Weight:134.08744 [g/mol]
Molecular Formula:C4H6O5
XLogP3:-1.3
H-Bond Donor:3
H-Bond Acceptor:5
Rotatable Bond Count:3
Exact Mass:134.021523
MonoIsotopic Mass:134.021523
Topological Polar Surface Area:94.8
Heavy Atom Count:9
Formal Charge:0
Complexity:129
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:1
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:5
Feature 3D Donor Count:1
Feature 3D Anion Count:2
Effective Rotor Count:3
Conformer Sampling RMSD:0.6
CID Conformer Count:13

Safety and Handling

【Hazard Codes】
Xi:Irritant
【Risk Statements】
R36/37/38
【Safety Statements 】
S26;S37/39
【Safety】

Hazard Codes:?IrritantXi
Risk Statements: 36/37/38?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36:Wear suitable protective clothing.?
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3
RTECS: ON7175000
HS Code: 29181980

【Skin, Eye, and Respiratory Irritations】
A skin and eye irritant
【Formulations/Preparations】
UVA URSI, THIS IS VOLATILE OIL CONTAINING A GLUCOSIDE, ARBUTIN, TANNIN, & GALLIC & MALIC ACIDS.
Grades: technical, active and inactive; FCC. The natural material is levorotatory, but the synthetic material is /optically/ inactive
Food grade: powder, fine granular, and granular
Granules and powder grades
【Exposure Standards and Regulations】
Substance added directly to human food affirmed as generally recognized as safe (GRAS).
Malic acid used as a general purpose food additive in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.
【Other Preventative Measures】
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
【Protective Equipment and Clothing】
A skin and eye irritant
【Specification】

Storage
It should be stored in a tightly closed container and keep container closed when not in use. It should be stored in a cool and dry area away from incompatible substances.
Handling
Wash thoroughly after handling.Avoid contact with eyes, skin, and clothing. Remove contaminated clothing and wash before reuse. Wash clothing before reuse. Avoid ingestion and inhalation. Use with adequate ventilation.
Personal Protection
Wear appropriate protective chemical safety goggles or eyeglasses. Wear appropriate protective gloves to prevent skin exposure.Wear suitable protective clothing to prevent skin exposure.
Small spills/leaks
Clean up spills right away, using the suitable protective equipment. Sweep up, then place into a container for disposal. Avoid generating dusty conditions. Provide ventilation.

【Octanol/Water Partition Coefficient】
log Octanol/water partition coefficient: -1.26
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

DL-MALIC ACID IS MFR BY HYDRATING MALIC & FUMARIC ACIDS IN PRESENCE OF SUITABLE CATALYSTS & SEPARATING MALIC ACID FROM EQUILIBRIUM PRODUCT MIXTURE. IN US ... NOWNTINUOUS PROCESS WHICH IS MUCH MORE ECONOMICAL THAN OLDER BATCH TYPE.
BY FERMENTATION FROM SUGARS.
MICROBIAL PRODUCTION OF L-FORM
Made synthetically by catalytic oxidation of benzene to maleic acid, which is converted to malic by heating with steam under pressure
Acid hydrolysis of acetoxysuccinic acid gave malic acid with retention of configuration at the asymmetric carbon atom
Bacterial, chemical, or electrochemical oxidation of glucose
By hydration of maleic anhydride
Isolated from natural sources by resolution of (R,S)-malic acid with the aid of an optically active base /(R)-(+)- and (S)-(-) malic acid/
Through the microbial fermentation of fumaric acid
Purification of malic /acid/ can be /performed/ by a two-stage crystallization process which first removes fumaric acid from the slurry and subsequently crystallizes washed malic acid after carbon and ion exchange treatment
U.S. Imports

(1983) Less than 4.54X10+8 g (est)
U.S. Production

(1984) 4.99X10+9 g (est)
Consumption Patterns

Dry beverage powders 50%; carbonated & still beverages, 25%; food & candy, 15%; metal cleaning & finishing, 5%; miscellaneous, 5% (1983)
【Usage】

Active ingredient in many sour or tart foods.

Biomedical Effects and Toxicity

【Biomedical Effects and Toxicity】
ORALLY OR IP ADMIN L- OR DL-MALIC ACID WAS EXTENSIVELY ELIMINATED AS CARBON DIOXIDE (83-92%). NO DIFFERENCES BETWEEN THE TWO FORMS WERE FOUND IN RATES (90-95% IN 24 HR) OR ROUTES OF EXCRETION. /L- & DL-MALIC ACID/

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: When released to soil, malic acid can be expected to biodegrade readily. The results of a number of biological screening tests have shown that malic acid is expected to biodegrade(1-6).
AQUATIC FATE: When released to natural water, malic acid can be expected to biodegrade readily. The results of a number of biological screening tests have shown that malic acid biodegrades(1-6). Aquatic volatilization, hydrolysis, bioconcentration and adsorption to sediment are not important environmental fate processes(SRC).
ATMOSPHERIC FATE: Based upon an estimated vapor pressure of 1.28X10-4 mm Hg at 25 deg C(1), malic acid could exist in both the vapor and particulate phases in the ambient atmosphere(2,SRC). It will degrade in the vapor phase by reaction with photochemically produced hydroxyl radicals at an estimated half-life rate of about 2 days(3,SRC). Malic acid has been detected in atmospheric particulate matter(4). Physical removal of particulate malic acid from air is likely is occur through wet and dry deposition(SRC).

Supplier Location

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